Patent GB-483368-A (GB)
Title: Process for protecting material containing keratin from the attack of textile pests
IPC: D06M19/00
Filed: 1936-09-14
Abstract: Fibrous material of animal origin, e.g. textiles, hides, leather, furs, and feathers is protected from attack by moths and other pests by incorporating therein an aromatic or heterocyclic compound having a substituent containing at least one quaternary nitrogen atom.  The substituent may contain one or more carbon atoms, and the carbon chain may be interrupted by O, S, SO2, N or P.  A preferred substituent is an aliphatic radicle containing at least 6 carbon atoms.  The compounds may be substituted by halogen, hydroxy, amino, sulpho, sulpho-ester, carboxylic acid, ether or thioether groups. Preferred compounds include (1) those made by reacting diphenyl derivatives, e.g. 4-hydroxy- or 4-amino-diphenyl with monochloro-triethylamine or 1.3-monochloro-propylamines and transforming the product with monochlorobenzyl chloride, dimethyl or diethyl sulphate into quaternary ammonium compounds; (2) derivatives of diphenyl- and triphenyl-methane, e.g. the condensation product of diethylamino-21-hydroxy-31.51-dichloro diphenylmethane and monochlorotriethylamine rendered quaternary with dimethyl sulphate, the condensation product of 1 mol. of 2.21-dihydroxy-3.31.5.51.4-pentachloro-triphenyl methane-211-sulphonic acid sodium salt with 2 mols. of monochlorotriethylamine rendered quaternary with dimethyl sulphate or dichlorobenzyl chloride, amides from substituted triphenylmethane sulphonic acids and substituted alkylene diamines rendered quaternary on the amine N-atom, such as the amide from N-methyl - N1 - dimethyl(ethyl) - ethylenediamine rendered quaternary with dimethyl sulphate; (3) heterocyclic compounds, e.g. condensation products of isatin with substituted phenols reacted with monochlorotriethylamine on the N-atom of the isatin and rendered quaternary on the amino N-atom; (4) products made by reacting acid amides with monochlorotriethylamine and subsequently rendering quaternary; (5) reaction products of acid chlorides and diamines or polyamines containing at least one N-atom which may be rendered quaternary; (6) cyclic organic compounds of the type RNIV where R is an aralkyl radicle and NIV is a quaternary nitrogen atom, e.g. benzyl-diethyldodecyl - ammonium chloride, 3.4-dichlorobenzyl - diethyl - dodecyl - ammonium chloride, xylyl - pyridinium chloride; menaphthylpyridinium chloride, bis-(3.4-dichloro-benzyl)-nicotinium chloride, di - (3.4 - dichlorobenzyl)-aminoethyltriethyl - ammonium sulphethylate, (3.4 - dichlorobenzyl methyl) - amino - ethyl-31.41 - dichlorobenzyl - dimethylammonium sulphomethylate, dibenzyl - dimethyl - di - (3.4-dichlorobenzyl) - trimethylene diammonium bromide.  The substances may be employed in solution in water or organic solvents, if desired at elevated temperatures.  The treatment may be applied during dyeing, soaping, rinsing, finishing, greasing or dry-cleaning or soaps containing the substances may be used. Fluorine compounds and alkaloids may be added.  Examples describe the treatment of materials with (1) the amide of 3.5.31.51-tetrachloro - 2.21 - dihydroxytriphenylmethane-211-sulphonic acid and d -(methyl-amino-pentyl)-diethyl - methyl - ammonium - sulphomethylate with the addition of sodium sulphate; (10) the amide of 3.5.31.51 - tetrachloro - 2.21 - diacetoxy - triphenylmethane - 211 - sulphonic acid and b -methylaminoethylethyltrimethyl ammonium sulphomethylate; the quaternary ammonium compounds from (2) 3.5.31.51.411-pentachloro-2.21 - bis - diethylaminoethylether triphenylmethane-211 sulphonic acid sodium salt and dimethyl sulphate; (3) 2.21 - diethyl - amino-ethylether-3.31-dimethyl-5.51.211 -trichlorotriphenyl methane and 2 mols. of 3.4-dichlorobenzyl chloride in the presence of sodium sulphate; (4) 2.21-diethylamino-ethylether-5.51-dichloro -diphenylmethane and 3.4-dichlorobenzyl chloride; (5) 21.41-diamino-diphenyl-2.4-dichlorobenzoyl chloride, monochlorotriethylamine and dimethyl sulphate; (6) 3-bis-(31.51-dichloro-21-hydroxy-phenyl) -1-diethyl-amino-ethyl-oxindol and p-chlorobenzyl chloride; (7) methyl - 2 - chloro - 4 - (diethylaminoethoxy)-diphenylmethane and 3.4 - dichloro - benzylchloride; (8) 1 mol. of 2.41-diaminodiphenyl, 2 mols. of monochlorotriethylamine and 1 mol. of 3.4-dichloro-benzyl chloride; (9) 4-diethylamino - diphenyl - methane - 31.51 - dichloro - 21-diethylaminoethyl ether and dimethyl sulphate; (11) 3.4.31.41-bis-(dichlorophenoxy) phosphorus sulphochloride, asymmetric diethylethylene diamine and 3.4-dichlorobenzyl chloride; (17) 3.4 - dichlorobenzene sulphomonomethylamide, monochlorotriethylamine and 3.4-dichlorobenzyl chloride.  Formul  for the above compounds are given.  Specification 471,404 is referred to.